12/14/14-Helix Formation in 2:1 α/β-Hybrid Peptides Containing Bicyclo[2.2.2]octane Ring Constraints

被引：7

作者：

Legrand, Baptiste ^{[1
]}

Andre, Christophe ^{[1
]}

Moulat, Laure ^{[1
]}

Didierjean, Claude ^{[2
]}

Hermet, Patrick ^{[3
]}

Bantignies, Jean-Louis ^{[4
]}

Martinez, Jean ^{[1
]}

Amblard, Muriel ^{[1
]}

Calmes, Monique ^{[1
]}

机构：

[1] Univ Montpellier, Inst Biomol Max Mousseron IBMM, CNRS, UMR 5247,ENSCM, 15 Ave Charles Flahault, F-34093 Montpellier 5, France

[2] Univ Lorraine, CNRS, UMR 7063, CRM2, Blvd Aiguilletes, F-54506 Vandoeuvre Les Nancy, France

[3] Univ Montpellier, Inst Charles Gerhardt Montpellier, CNRS, UMR 5253,ENSCM, Pl E Bataillon, F-34095 Montpellier 5, France

[4] Univ Montpellier, Lab Charles Coulomb, CNRS, UMR 5221, F-34095 Montpellier, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 34期

关键词：

12/14/14-helix; bicyclic beta-amino acids; helical structures; structure elucidation; alpha/beta-hybrid peptides; BETA-AMINO ACID; HELICAL SECONDARY STRUCTURES; CRYSTALLOGRAPHIC CHARACTERIZATION; STRUCTURAL-CHARACTERIZATION; HETEROGENEOUS BACKBONES; FOLDAMERS; RESIDUES; DESIGN; CONFORMATIONS; ALPHA; BETA;

D O I：

10.1002/chem.201602746

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly constrained beta-amino acid ABOC induces different types of helices in beta urea and 1:1 alpha/beta amide oligomers. The latter can adopt 11/9- and 18/16-helical folds depending on the chain length in solution. Short peptides alternating proteinogenic alpha-amino acids and ABOC in a 2: 1 alpha/beta repeat pattern adopted an unprecedented and stable 12/14/14-helix. The structure was established through extensive NMR, molecular dynamics, and IR studies. While the 1: 1 alpha-AA/ABOC helices diverged from the canonical alpha-helix, the helix formed by the 9-mer 2: 1 alpha/beta-peptide allowed the projection of the alpha-amino acid side chains in a spatial arrangement according to the alpha-helix. Such a finding constitutes an important step toward the conception of functional tools that use the ABOC residue as a potent helix inducer for biological applications.

引用

页码：11986 / 11990

页数：5

共 47 条

[31] NEW 2,3-DIHYDRO-5H-1,4-BENZODIOXEPIN DERIVATIVES - EASY FORMATION AND X-RAY STRUCTURE DETERMINATION OF A PENTACYCLIC ACETAL CONTAINING A 14-MEMBERED CARBON-OXYGEN RING
LUCCHESINI, F
BERTINI, V
POCCI, M
DEMUNNO, G
CRISPINI, A
TETRAHEDRON, 1995, 51 (35) : 9757 - 9766
[32] The crystal structure of condensed ring compounds. VI. 1:2-benzanthracene C18H12, 5-methyl-1 : 2-benzanthracene C19H14 and 3-methyl-1 : 2-benzanthraquinone C19H12O2.
Iball, J
ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1938, 99 (03): : 230 - 237
[33] DISPROPORTIONATION OF THE CYCLOOCTENE LIGAND IN THE REACTION OF [IRCL(C8H14)2]2- WITH AGOCOCF3 - FORMATION OF [IR(OCOCF3)(C8H14)2]2 AND [IR(OCOCF3)(1,5-C8H12)]2 AND THEIR CONVERSION INTO CATIONIC ARENE COMPLEXES
BIANCHI, F
GALLAZZI, MC
PORRI, L
DIVERSI, P
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 202 (01) : 99 - 105
[34] Crystal structure of (1R,4S,5R,7R)-4-bromomethyl-4-methyl-3,6,8-trioxa-2-oxo-bicyclo[3.2.1]octane-7-dimethylcarboxamide, C10H14BrNO5
Peters, K
Peters, EM
vonSchnering, HG
Kuhn, B
Jager, V
ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1996, 211 (04): : 269 - 270
[35] Time-controlled synthesis of the 3D coordination polymer U(1,2,3-Hbtc)2 followed by the formation of molecular poly-oxo cluster {U14} containing hemimellitate uranium(iv)
Dufaye, Maxime
Martin, Nicolas P.
Duval, Sylvain
Volkringer, Christophe
Ikeda-Ohno, Atsushi
Loiseau, Thierry
RSC ADVANCES, 2019, 9 (40) : 22795 - 22804
[36] Crystal structure of 1,19(1,3,2),10,28(1,2)-tetrabenzena-3,6,9,11,14,17,21,24,27,29,32,35-dodecaoxa-37,38-dithio-bicyclo[17.17.2]hexatriacontaphane, C44H54O12S2
Nabeshima, T
Nishida, D
Horn, E
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2001, 216 (01): : 80 - 82
[37] RESEARCH ON NITROGEN CONTAINING HETEROCYCLIC-COMPOUNDS .14. DERIVATIVES OF 5H-PYRROLO[1,2-B][1,2,5]BENZOTRIAZEPINE, A NOVEL TRICYCLIC RING-SYSTEM, BY INTRAMOLECULAR CYCLIZATION OF N-ARYL-1H-PYRROL-1-AMINES
STEFANCICH, G
ARTICO, M
CORELLI, F
MASSA, S
SYNTHESIS-STUTTGART, 1983, (09): : 757 - 759
[38] [Ni(1,2-PDA)3]2(HOCH2CH2CH2NH3)3(H3O)2 [Ge7O14X3]3 (X = F, OH):: A new 1D germanate with 12-ring hexagonal tubular channels
Pan, Qinhe
Li, Jiyang
Ren, Xiaoyan
Wang, Zhuopeng
Li, Guanghua
Yu, Jihong
Xu, Ruren
CHEMISTRY OF MATERIALS, 2008, 20 (02) : 370 - 372
[39] SYNTHESIS AND MASS-SPECTRAL STUDIES OF FLUORINE CONTAINING 5A, 7B, 12A, 14B-TETRAHYDROBISINDOLO [2,3-B-2',3'-B'] BENZO [1,2-D-4,5-D'] DIFURANS
JOSHI, KC
PATHAK, VN
GUPTA, R
JOURNAL OF FLUORINE CHEMISTRY, 1988, 38 (02) : 153 - 161
[40] POLYOXOMETALATES CATALYST MATERIALS - X-RAY THERMAL-STABILITY STUDY OF PHOSPHORUS-CONTAINING HETEROPOLYACIDS H3+XPM12-XVXO40.13-14H2O (M = MO,W - X = 0-1)
FOURNIER, M
FEUMIJANTOU, C
RABIA, C
HERVE, G
LAUNAY, S
JOURNAL OF MATERIALS CHEMISTRY, 1992, 2 (09) : 971 - 978

← 1 2 3 4 5 →